Occasionally we get a print job which makes CUPS break, and it takes
the
printer offline until the job is deleted and an admin logs in and
restarts the queue. I would like monit to keep an eye on this and when
it happens, clear the print queue and restart the printer
automatically.

I do this without monit. Run a script from cron every x minutes. If it detects
an offline printer, it restarts cups and only then generates output/sends an
email.

Thanks for the suggestion, this works well. For reference, this is the
script I run from cron every couple of minutes: